This invention is for a process for production of 5-(alkyl or haloalkyl)-2-iminooxazolidines and thiazolidines. These compounds may be represented by the general formula ##STR2## in which R.sub.1 represents an optionally substituted phenyl ring, R.sub.2 is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 haloalkyl and W is oxygen or sulfur. Compounds of this general type have been described in the prior art, for instance in U.S. Pat. No. 4,665,083 (iminothiazolidines) and a paper by Mateev et al., Chemical Abstracts, Vol. 76, No. 153651 g (1972) (production of 2-imino-3-phenyl-5-chloromethyl-1,3-oxazolidine). Iminothiazolidines of this type are also disclosed as intermediates for substituted 2-iminothiazolidines in U.S. patent applications Nos. 214,348 and 214,347 of Frank X. Woolard, entitled "2-(Acylimino)thiazolidine Herbicides" and "Novel Herbicidal 2-Sulfonyliminothiazolidines", filed concurrently herewith.
U.S. Pat. No. 4,665,083 discloses a number of processes for preparing such compounds including cyclization of an isocyanate, cyclization of a thiourea, and reaction of an iminothiazolidine with an aromatic fluoride. Mateev et al. disclose reaction of phenyl cyanamide with epichlorohydrin to produce a nearly 50/50 mixture of 2-imino-3-phenyl-5-chloromethyl-1,3-oxazolidine and 2-N-phenylimino-5-chloromethyl-1,3-oxazolidine, as well as corresponding butyl compounds produced from butyl cyanamide.